Amiphenazole

Amiphenazole
Clinical data
ATC code	none;
Legal status
Legal status	AU: S4 (Prescription only);
Identifiers
	IUPAC name 5-phenyl-1,3-thiazole-2,4-diamine;
CAS Number	490-55-1;
PubChem CID	10275;
ChemSpider	9855 ;
UNII	7ZJ8PWY0XD;
ChEMBL	ChEMBL1514085;
CompTox Dashboard (EPA)	DTXSID7046388 ;
ECHA InfoCard	100.007.013
Chemical and physical data
Formula	C9H9N3S
Molar mass	191.25 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C2=C(N=C(S2)N)N;
	InChI InChI=1S/C9H9N3S/c10-8-7(13-9(11)12-8)6-4-2-1-3-5-6/h1-5H,10H2,(H2,11,12) ; Key:UPOYFZYFGWBUKL-UHFFFAOYSA-N ;
	(verify)

Amiphenazole (Daptazile) is a respiratory stimulant traditionally used as an antidote for barbiturate or opiate overdose, usually in combination with bemegride,^[1]^[2] as well as poisoning from other sedative drugs^[3]^[4] and treatment of respiratory failure from other causes.^[5] It was considered particularly useful as it could counteract the sedation and respiratory depression produced by morphine but with less effect on analgesia.^[6]^[7] It is still rarely used in medicine in some countries, although it has largely been replaced by more effective respiratory stimulants such as doxapram and specific opioid antagonists such as naloxone.^[8]^[9]

References

^ Worlock A (November 1956). "Barbiturate poisoning treated with amiphenazole and bemegride". British Medical Journal. 2 (5001): 1099–101. doi:10.1136/bmj.2.5001.1099. PMC 2035840. PMID 13364395.
^ Mears GW (March 1958). "Massive doses of bemegride and amiphenazole in treatment of barbiturate poisoning". British Medical Journal. 1 (5073): 757–8. doi:10.1136/bmj.1.5073.757. PMC 2028148. PMID 13510792.
^ Dotevall G, Herner B (August 1957). "Treatment of acute primidone poisoning with bemegride and amiphenazole". British Medical Journal. 2 (5042): 451–2. doi:10.1136/bmj.2.5042.451. PMC 1961943. PMID 13446511.
^ Rowell NR (February 1957). "Treatment of glutethimide poisoning with bemegride and amiphenazole". Lancet. 272 (6965): 407–9. doi:10.1016/s0140-6736(57)90466-x. PMID 13407028.
^ Little GM (January 1962). "Use of amiphenazole in respiratory failure". British Medical Journal. 1 (5273): 223–6. doi:10.1136/bmj.1.5273.223. PMC 1957266. PMID 14465883.
^ Mckeogh J, Shaw FH (January 1956). "Further experience with amiphenazole and morphine in intractable pain". British Medical Journal. 1 (4959): 142–4. doi:10.1136/bmj.1.4959.142. PMC 1978927. PMID 13276651.
^ Gershon S, Bruce DW, Orchard N, Shaw FH (August 1958). "Amiphenazole and morphine in production of analgesia". British Medical Journal. 2 (5092): 366–8. doi:10.1136/bmj.2.5092.366. PMC 2025982. PMID 13560868.
^ Gairola RL, Gupta PK, Pandley K (January 1980). "Antagonists of morphine-induced respiratory depression. A study in postoperative patients". Anaesthesia. 35 (1): 17–21. doi:10.1111/j.1365-2044.1980.tb03714.x. PMID 6994518. S2CID 40955560.
^ O'Neill WM (1994). "The cognitive and psychomotor effects of opioid drugs in cancer pain management". Cancer Surveys. 21: 67–84. PMID 8565000.

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[1] Worlock A (November 1956). "Barbiturate poisoning treated with amiphenazole and bemegride". British Medical Journal. 2 (5001): 1099–101. doi:10.1136/bmj.2.5001.1099. PMC 2035840. PMID 13364395.

[2] Mears GW (March 1958). "Massive doses of bemegride and amiphenazole in treatment of barbiturate poisoning". British Medical Journal. 1 (5073): 757–8. doi:10.1136/bmj.1.5073.757. PMC 2028148. PMID 13510792.

[3] Dotevall G, Herner B (August 1957). "Treatment of acute primidone poisoning with bemegride and amiphenazole". British Medical Journal. 2 (5042): 451–2. doi:10.1136/bmj.2.5042.451. PMC 1961943. PMID 13446511.

[4] Rowell NR (February 1957). "Treatment of glutethimide poisoning with bemegride and amiphenazole". Lancet. 272 (6965): 407–9. doi:10.1016/s0140-6736(57)90466-x. PMID 13407028.

[5] Little GM (January 1962). "Use of amiphenazole in respiratory failure". British Medical Journal. 1 (5273): 223–6. doi:10.1136/bmj.1.5273.223. PMC 1957266. PMID 14465883.

[6] Mckeogh J, Shaw FH (January 1956). "Further experience with amiphenazole and morphine in intractable pain". British Medical Journal. 1 (4959): 142–4. doi:10.1136/bmj.1.4959.142. PMC 1978927. PMID 13276651.

[7] Gershon S, Bruce DW, Orchard N, Shaw FH (August 1958). "Amiphenazole and morphine in production of analgesia". British Medical Journal. 2 (5092): 366–8. doi:10.1136/bmj.2.5092.366. PMC 2025982. PMID 13560868.

[8] Gairola RL, Gupta PK, Pandley K (January 1980). "Antagonists of morphine-induced respiratory depression. A study in postoperative patients". Anaesthesia. 35 (1): 17–21. doi:10.1111/j.1365-2044.1980.tb03714.x. PMID 6994518. S2CID 40955560.

[9] O'Neill WM (1994). "The cognitive and psychomotor effects of opioid drugs in cancer pain management". Cancer Surveys. 21: 67–84. PMID 8565000.

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Clinical data

ATC code	none
Legal status
Legal status	AU: S4 (Prescription only)
Identifiers
IUPAC name 5-phenyl-1,3-thiazole-2,4-diamine
CAS Number	490-55-1
PubChem CID	10275
ChemSpider	9855^Y
UNII	7ZJ8PWY0XD
ChEMBL	ChEMBL1514085
CompTox Dashboard (EPA)	DTXSID7046388
ECHA InfoCard	100.007.013
Chemical and physical data
Formula	C₉H₉N₃S
Molar mass	191.25 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C2=C(N=C(S2)N)N
InChI InChI=1S/C9H9N3S/c10-8-7(13-9(11)12-8)6-4-2-1-3-5-6/h1-5H,10H2,(H2,11,12)^Y Key:UPOYFZYFGWBUKL-UHFFFAOYSA-N^Y
(verify)